毕赤血水草 A-E，双吲哚生物碱来自（Nees）Bremek. 的叶子。

Baphicacanthcusines A-E, Bisindole Alkaloids from the Leaves of (Nees) Bremek.

机构信息

Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.

College of Pharmaceutical Sciences, Hebei University, Baoding 071002, China.

出版信息

J Org Chem. 2020 Jul 2;85(13):8580-8587. doi: 10.1021/acs.joc.0c00949. Epub 2020 Jun 16.

DOI:10.1021/acs.joc.0c00949

PMID:32501005

Abstract

Four pairs of stereoisomeric indole alkaloids, (±)-baphicacanthcusines A-D (), and one new indole alkaloid, baphicacanthcusine E (), together with nine known compounds were identified from the leaves of . (±)- and - possess an unprecedented skeleton in which two indole moieties are bridged by a phenylpropane unit. (±)- represents the first natural dispiro-oxazolidinone bisoxindoles. The absolute configurations in were assigned based on quantum chemical calculations, including the calculated chemical shift with DP4plus analysis, the calculated optical rotation values, and the calculated electronic circular dichroism spectra. A plausible biosynthetic pathway for was proposed. Compounds (±)-, (-)-, and exhibited cytotoxicity against MCF-7 cells with IC values of 20.0-78.5 μM.

摘要

从中鉴定出四对立体异构吲哚生物碱（±）-baphicacanthcusines A-D () 和一种新的吲哚生物碱 baphicacanthcusine E ()，以及九种已知化合物。(±)- 和 - 具有前所未有的骨架，其中两个吲哚部分由苯丙烷单元桥接。(±)- 代表第一个天然双螺-恶唑烷酮双氧化吲哚。根据量子化学计算，包括 DP4plus 分析计算的化学位移、计算的旋光值和计算的电子圆二色谱谱，确定了在中的绝对构型。提出了的可能生物合成途径。化合物 (±)-、(-)- 和对 MCF-7 细胞表现出细胞毒性，IC 值为 20.0-78.5 μM。